Uefa Cup: Bolton manager Sam Allardyce is contemplating a daunting trip to Istanbul after his side's Uefa Cup group stage opponents were confirmed at the draw in Nyon yesterday.
Allardyce learned his side's first European campaign will take them to the Turkish city to face Besiktas on October 20th as well as Portugal's Guimaraes on November 24th.
Bolton will also face both the Russians of Zenit St Petersburg and Spanish giants Sevilla at the Reebok Stadium on November 3rd and December 15th respectively.
Ahead of their October 20th trip to a team currently standing seventh in the Turkish league, Allardyce said: "Playing in Istanbul is always very tricky - Besiktas will be a tough match for us and many English clubs have found it difficult in Turkey in the past.
"With it being the first game of the group it will be important to get off to a good start and we will do our homework and prepare in the right manner."
Otherwise Bolton were relatively fortunate with the draw which enabled them to avoid a gruelling trip to Russia and also set up the appetising home tie with Sevilla.
Middlesbrough face tough trips to Grasshoppers of Zurich and Holland's AZ Alkmaar, with Dnipro and Litex Lovech visiting the Riverside Stadium.
The meeting with last season's semi-finalists Alkmaar, who are managed by former Ajax, Barcelona and Holland coach Louis van Gaal, looks the toughest.
But Dnipro's 5-1 defeat of former Boro defender Tony Mowbray's Hibernian side will not have got unnoticed on Teesside.
Middlesbrough, who reached the final 16 last season before going out to beaten finalists Sporting Lisbon, will open their latest campaign with a trip to Zurich on October 20th before entertaining Dnipro on November 3rd.
They then head for the Netherlands on November 24th before bringing down the curtain on Group D with the visit of Bulgarian side Litex to the Riverside on December 15th.
GROUP A: Monaco (Fra), Slavia Prague (Cze), Hamburg SV (Ger), CSKA Sofia (Bul), Viking Stavanger (Nor).
GROUP B: Lokomotiv Moscow (Rus), Espanyol (Spa), Palermo (Ita), Brondby (Den), Maccabi Petah Tikva (Isr).
GROUP C: Hertha Berlin (Ger), Racing Lens (Fra), Sampdoria (Ita), Steaua Bucharest (Rom), Halmstad (Swe).
Group D: AZ Alkmaar (Ned), Middlesbrough (Eng), Dnipro Dnipropetrovsk (Ukr), Grasshoppers (Swi), Litex Lovech (Bul).
GROUP E: AS Roma (Ita), Basel (Swi), Red Star Belgrade (Serb & Mont), Racing Strasbourg (Fra), Tromso (Nor).
Group F: CSKA Moscow (Russia), Olympique Marseille (France), Heerenveen (Netherlands), Levski Sofia (Bulgaria), Dinamo Bucharest (Romania).
GROUP G: VfB Stuttgart (Ger), PAOK Salonika (Gre), Shakhtar Donetsk (Ukr), Stade Rennes (Fra), Rapid Bucharest (Rom).
GROUP H: Besiktas (Tur), Sevilla (Spa), Bolton Wanderers (Eng), Zenit St Petersburg (Rus), Vitoria Guimaraes (Por).
